Chicago to Anywhere Flights

Canada is typically the cheapest at $324 but deals to United States are $225 right now.
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Best Deals from MDW

Discover the cheapest current deals from 2,386 recent searches matching your trip
  • $307
    Mexico City
    9 days in Jan & Feb
    Wed
    23
    Fri
    1
  • $764
    Los Angeles
    2 days in Aug
    Sat
    25
    Mon
    27
  • $469
    Puerto Vallarta
    4 days in Feb
    Thu
    14
    Mon
    18
  • $855
    Paris
    8 days in Oct & Nov
    Mon
    29
    Tue
    6
  • $877
    Orlando
    3 days in Aug
    Fri
    17
    Mon
    20
  • $381
    Cancun
    3 days in Jul
    Sat
    21
    Tue
    24
  • When to Fly
    Prices range from $555 in August to $1,130 in May
  • Mexico and Central America
    $307
    Whoa, this is 53% off
  • United States
    $225
    Whoa, this is 63% off
  • Europe
    $681
    Whoa, this is 58% off
  • Canada
    $247
    This is a good deal at 24% off
  • Asia
    $773
    Whoa, this is 70% off
  • Africa
    $1,799
    This is a good deal at 24% off
  • From:
    Chicago (MDW)
        
    To:
    Anywhere    
        
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